Robert P. Rudolph

Overview

Bobby represents individuals and businesses in complex commercial litigation. His cases involve issues related to business, employment, real estate and construction. Bobby is a trusted advisor on pre-litigation issues, regularly appears in court and has successfully resolved a range of matters through alternative dispute resolution.

In addition to general corporate disputes, Bobby litigates highly contentious shareholder disputes between owners of closely held businesses. His clients rely on him to counsel them through claims involving breach of contract, corporate opportunity, fraud and freeze-out, often with millions of dollars and control of well-known companies on the line.

Bobby’s employment law practice encompasses federal and state wage and hour issues, wrongful termination, discrimination, harassment and retaliation claims, independent contractor misclassifications and non-compete issues. He litigates matters in court and at arbitrations and represents clients before the Massachusetts Commission Against Discrimination and the Equal Employment Opportunity Commission. Bobby also defends companies subject to investigation by government agencies, including the U.S. Department of Labor, the U.S Department of Homeland Security’s Immigration and Customs Enforcement Division and the Massachusetts Office of the Attorney General. For corporate clients, Bobby serves as an experienced resource to management when employment issues arise, and he routinely drafts and reviews employment handbooks, policies and agreements.

Working with property owners, developers, contractors and material suppliers, Bobby handles a diverse range of real estate and construction related issues, including disagreements with abutters and construction disputes. He regularly asserts mechanic’s liens and bond claims to recover unpaid amounts due to contractors and material suppliers. Additionally, Bobby litigates condominium disputes and landlord/tenant issues. He is experienced with condominium bylaws, special assessments and capital projects and formerly served as Chair of the Board of Trustees of a 374-unit Boston high-rise.

Experience

Business

• Assisted in the successful defense of a contempt action brought by the Office of the Attorney General against three corporate entities and their principal after a nine-day bench trial in Suffolk Superior Court.
• Part of a trial team that obtained the dismissal of claims against a professional services firm after an eight-day jury trial in the Business Litigation Session of Suffolk Superior Court.
• Represented clients in a variety of highly contested disputes between shareholders of closely held businesses (retail, hospitality, real estate, manufacturing, distribution, etc.); claims included breach of contract, breach of fiduciary duty, fraud and corporate freeze-outs.
• Represented a real estate developer in a lawsuit for enforcement of an out-of-state judgment in a contract dispute over breach of multiple commercial leases, helping the client recover $3.8 million.
• Represented the operator of a cannabis cultivation center in its appeal before the Massachusetts Land Court of the denial of its special permit application by the city’s municipal council, obtaining issuance of the special permit.
• Obtained a court order on behalf of a prominent retail business ordering that a competing business promptly change its name and permanently cease and desist from using certain terms in its new name and promotional materials.
• Obtained favorable outcomes in multiple wrongful death actions, resulting in substantial monetary payments and a $4 million judgment in a matter involving the death of an infant.
• Represented various restaurant clients before the City of Boston Licensing Board and other local municipal licensing boards for liquor license permitting, license amendments and hearings for citations related to the service of alcohol.

Employment

• Served as co-trial counsel and obtained a defense verdict after a four-day jury trial in Suffolk Superior Court for a group of national restaurants on all counts in a lawsuit involving wrongful termination and discrimination claims.
• Represented a national mortgage lender in a lawsuit against its former Executive Vice President, the EVP’s new competing company and its publicly traded parent company for misappropriation of trade secrets and breach of fiduciary. Obtained a preliminary injunction and a significant settlement payment for the client, resulting in closure of the competing business.
• Represented an employer in a lawsuit against its former employee who stole nearly $400,000 from the employer. Obtained a court order freezing the former employee’s bank accounts and attaching his real estate. Recovered all stolen funds and attorney’s fees for the client.
• Obtained a dismissal of a whistleblower complaint filed with the U.S. Department of Labor, Occupational Safety and Health Administration claiming use of retaliatory employment practices in violation of the U.S. Food and Drug Administration’s Whistleblower Provisions.
• Represented clients in investigations conducted by the United States Department of Labor, Office of the Attorney General of Massachusetts and Department of Homeland Security, Immigration and Customs Enforcement Division (Form I-9 Investigation).
• Successfully defended employers before the Massachusetts Commission Against Discrimination and the Equal Employment Opportunity Commission from claims alleging discrimination and wrongful termination based on gender, race, pregnancy, sexual orientation, sexual harassment, disability, religion and retaliation.
• Collected unpaid wages, treble damages and attorney’s fees on behalf of employees.
• Represented an employee terminated by a Fortune 500 company the day after requesting medical leave, resulting in a favorable resolution for the employee’s claim filed with the Massachusetts Commission Against Discrimination.
• Represented an employee constructively terminated for refusing sexual advances by her superior, resulting in a favorable resolution of the employee’s claim filed with the Massachusetts Commission Against Discrimination.

Real Estate/Construction

• Represented the owner of residential property valued at more than $2 million in an emergency motion to dissolve a memorandum of lis pendens and a special motion to dismiss; both motions were granted within two days of filing, the client was awarded its costs and fees in full, and the owner of the home was able to proceed with the sale of the property
• Obtained summary judgment on behalf of a Back-Bay condominium owner who was improperly assessed a portion of a condominium’s special assessment to rebuild its parking garage. On appeal by the condominium, represented the owner before the Massachusetts Court of Appeals, which affirmed the judgment in favor of the owner.
• Obtained an Arbitrator’s Award in favor of a condominium unit owner declaring that the client’s fence was properly installed on exclusive use areas, not common areas, as claimed by another unit owner.
• Recovered a substantial settlement for a condominium unit owner in a lawsuit against the Trustees of the condominium for failing to promptly repair leaking common area pipes and temporarily rendering the owner’s unit uninhabitable.
• Represented the operator of a marijuana cultivation center in a lawsuit against a third-party purported holder of a right of first refusal on the property seeking to prevent the development of the property. Obtained a full waiver of all purported restrictions and rights claimed by the third-party on the property.
• Represented a property owner and its tenant in a dispute with a general contractor and subcontractor over substantial defects in a multi-million-dollar office renovation project.
• Represented a contractor in a dispute with its insurance carrier over damage to its work by a sub-sub-contractor. Obtained full payment of the claim, more than $500,000.
• Assisted in the judicial appeal of the City of Boston Zoning Board of Appeal’s denial of a conditional use permit for a real estate development and obtained a court order overruling the ZBA’s decision and ordering the conditional use permit and building permit for the project to be issued immediately with no conditions.
• Represented a landlord in a matter involving claims of violations of the Massachusetts Security Deposit Law and a U.S. Department of Housing Section 8 Tenant-Based Housing Assistance Payments Contract.
• Represented multiple owners, contractors and material suppliers in matters involving mechanic’s liens asserted pursuant to the Massachusetts Mechanics Lien Law and bond claims, recovering millions of dollars on behalf of contractors and material suppliers.
• Successfully represented a large national bank in opposition to an emergency motion for a temporary restraining order filed in the eleventh-hour as an attempt to prevent foreclosure of a commercial property.
• Obtained a Memorandum of Lis Pendens on behalf of a property buyer, preventing the seller from transferring the property to a third-party buyer for a higher price, and ultimately assisting the client buyer in consummating its purchase of the property.
• Defended a landlord from claims asserted by a tenant of violation of the Massachusetts Security Deposit Law and Massachusetts Sanitary Code.
• Represented a landlord in a lawsuit against a tenant for breach of a lease, recovering lost rent for the landlord.
• Represented a condominium unit owner in opposition to condominium’s proposal to replace the condominium’s HVAC system, successfully preventing the condominium’s plan from moving forward.
• Represented property owners and developers in matters involving construction defects, including the defense of a developer of a Boston condominium project from claims of construction defects asserted by the condominium trust and certain individual unit owners, and the representation of a high-end waterfront homeowner in a lawsuit against the manufacturer of custom windows due to defects and leaks.
• Represented general contractors in investigations conducted by OSHA as a result of serious workplace accidents, including the successful contest of citations issued by OSHA resulting in full withdrawal of the citations and penalties.

Accolades

• Best Lawyers in America©: Ones to Watch, Commercial Litigation (2024 and 2025); Litigation – Labor and Employment (2025) and Labor and Employment Law – Employee (2021 and 2022)
• Massachusetts Super Lawyers, 2024
• Rising Star, Massachusetts Super Lawyers, 2014 – 2022
• Daniel R. Ginsberg National Leadership Award (awarded by the Anti-Defamation League), 2020
• Krupp Leadership Award (awarded by the Anti-Defamation League), 2015

Associations & Memberships

• Boston Wharf District Council
  Board of Directors, Executive Committee and Voting Member, 2024 – Present
• Anti-Defamation League
  New England Regional Board Member, 2018 – Present
  Co-Chair, Associate Board, 2015 – 2017
  Associate Board Member, 2013 – 2023
  Glass Leadership Institute, 2013
• Board of Trustees of a 374-unit Condominium Building
  Chair, 2016 – 2021
  Vice-Chair, 2015 – 2016
• Associated Builders and Contractors of Massachusetts
  Young Leaders Council, 2013 – 2018
• The Governor’s Academy
  Class Agent
• Massachusetts Bar Association, Member

Publications & Events

• Profit-Sharing Arrangement Not a “Wage” Under the Massachusetts Wage Act
• Minority Shareholders Owe a Fiduciary Duty to One Another and the Corporation
• Condominium Trust Has Duty of Care to Protect Residents from Crimes
• Appeals Court Takes New Stance on “Pay Under Protest” Principle for Challenging Improperly Imposed Condominium Late Fees and Fines
• Conducting Employee Interviews – Ask the Right Questions or Face Litigation
• Massachusetts Employers – It’s Time to Update Your Employee Handbooks
• Since Covid-19, Many More Mechanic’s Liens Filed
• Bracing for COVID-19 Litigation – What to Expect and How to Avoid It
• Legal Considerations Regarding Coronavirus (COVID-19)
• Reminder: Important Wage & Hour Updates Effective January 1, 2020
• Authorized Employees? Form I-9 Non-Compliance Risks
• Department of Labor Modifies Stance on Obama Era 80/20 Rule for Tipped Employees
• Security Deposits: Could They Be More Harmful Than Helpful?
• Caution to Employers: When Paid Administrative Leave Constitutes Unlawful Retaliation
• Franchisor Not Liable for Alleged Tips Act Violation by Franchisee
• Robert Rudolph and Adam Shafran Present Employment Law Seminar on November 8
• Land Court Rules No Binding Agreement Where Broker Lacks Authority to Bind Seller
• When Children Become Adults: 3 Essential Legal Documents
• Landowner Liable When Guest Walks into Area Marked “Employees Only”
• Court Denies Former CEO Access to Privileged Communications
• Constructive Knowledge of Overtime Work Sufficient for Wage Act Liability
• Massachusetts Finalizes Earned Sick Time Regulations
• Rudolph Friedmann Law Firm Obtains Millions For Massachusetts Trash Haulers
• RF’s Ashley Green Talks Hernandez on Kiss 108’s “Matty in the Morning”
• Massachusetts Becomes Fourth State to Enact Domestic Worker’s Bill of Rights
• Nine RF Attorneys Named 2014 Massachusetts Super Lawyers and Rising Stars
• Tip Pooling: Know the Law in Massachusetts
• Enforceability of Covenants Not To Compete: Employers Win and Lose
• Firm News
• No Signed Lease, Yet Broker’s Fee Must Be Paid

• Since COVID-19, Many More Mechanic’s Liens Filed
• Bracing for COVID-19 Litigation – What to Expect and How to Avoid It
• Legal Considerations Regarding Coronavirus (COVID-19)
• Reminder: Important Wage & Hour Updates Effective January 1, 2020
• Authorized Employees? Form I-9 Non-Compliance Risks
• Security Deposits: Could They Be More Harmful Than Helpful?
• Department of Labor Modifies Stance on Obama Era 80/20 Rule for Tipped Employees
• Caution to Employers: When Paid Administrative Leave Constitutes Unlawful Retaliation
• Franchisor Not Liable for Alleged Tips Act Violation by Franchisee
• Land Court Rules No Binding Agreement Where Broker Lacks Authority to Bind Seller
• When Children Become Adults: 3 Essential Legal Documents
• Landowner Liable When Guest Walks into Area Marked “Employees Only”
• Court Denies Former CEO Access to Privileged Communications
• New Case Establishes Liability for Boston Restaurant Owners with Multiple Locations
• Constructive Knowledge of Overtime Work Sufficient for Wage Act Liability
• Massachusetts Finalizes Earned Sick Time Regulations
• Massachusetts Becomes Fourth State to Enact Domestic Worker’s Bill of Rights
• Tip Pooling: Know the Law in Massachusetts
• No Signed Lease, Yet Broker’s Fee Must Be Paid
• Contractor’s Liens and Bonds – How to Get Paid Promptly on Construction Projects, Associated Builders and Contractors of Massachusetts, June 1, 2023
• New Developments in Employment Law, Associated Builders and Contractors of Massachusetts, June 12, 2018
• Do This, Not That: Navigating Complex Legal Employment Issues in the Construction Industry, Associated Builders and Contractors of Massachusetts, November 8, 2017
• Do This, Not That: Navigating Complex Legal Employment Issues in the Food and Beverage Industry, The Massachusetts Restaurant Association, February 15, 2017